Acetic Acid → HCID 118939112, compound

HRID 524007Notes

Reaction equation

HRID 524007 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[NH:10][CH2:9][CH2:8][C:7]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:6]1=2)=[O:4].Cl.[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]([NH:27][C:28](=[O:30])[CH3:29])[CH3:26])=[CH:21][CH:20]=1)=O.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[C:6]2[C:7](=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH2:8][CH2:9][N:10]1[CH2:17][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]([NH:27][C:28](=[O:30])[CH3:29])[CH3:26])=[CH:23][CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2759853Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate--hydrogen chloride (1/1)HCID 5049666Sodium triacetoxyborohydrideHCID 118939068HCID 118939068, compound

Product 1

HCID 118939112HCID 118939112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 mg (0.821 mmol) 7-hydroxy-1,2,3,4-tetrahydro-3-isoquinoline-4-carboxylic acid methyl ester hydrochloride and 157 mg (0.821 mmol) (S)—N-(1-(4-formylphenyl) ethyl) acetamide (example III) in 5 mL THF are added 141 μL (2.46 mmol) AcOH and the mixture is stirred at r.t. for 10 min. After that time, the resulting mixture is cooled to 0° C., 261 mg (1.23 mmol) sodium triacetoxyborohydride are added and the reaction mixture is stirred at r.t. for 2 h. After that time, the reaction is quenched by addition of 500 μL water and purified by HPLC (ACN/H2O/NH3).

Workup

  1. temperatureAfter that time, the resulting mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at r.t. for 2 h
  3. customAfter that time, the reaction is quenched by addition of 500 μL water
  4. custompurified by HPLC (ACN/H2O/NH3)

Sources & evidence

ORD record
ord-b877e72fd96d474db508eab15441da1b
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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